Ethanol → Benzeneacetic acid, 2,4-dihydroxy-alpha-oxo-, ethyl ester

To a solution of resorcinol (5.0 g, 45.4 mmol, 1 eq) in diethyl ether (30 mL) was added 3M EtMgBr (18.5 mL, 50.0 mmol, 1.1 eq)) dropwise under argon. The reaction mixture was stirred at rt for 20 min. The ether was removed under vacuum and anhydrous toluene (80 mL) was added. A solution of oxalyl chloride (4.36 mL, 50 mmol, 1.1 eq) in toluene (20 mL) was added to the mixture dropwise under argon. The reaction mixture was stirred at rt for 15 h. Anhydrous ethanol (40 mL) was added to the mixture and the reaction mixture was stirred at rt for 1 h. Most of the solvent was evaporated and then EtOAc (60 mL) and water (40 mL) were added to the mixture. The layer was separated and the organic layer was washed with water (2×40 mL), dried over Na2SO4, filtrated, and concentrated under reduced pressure. The residue was purified by column chromatography eluted with 20% EtOAc/hexane then 50% EtOAc/hexane solution to afford white solid (5.88 g, 62%) as product. 1H-NMR (CD3CN): δ 7.62(d, J=9.0 Hz, 1H), 6.50 (dd, J=2.3, 9.0 Hz, 1H), 6.41 (d, J=2.3 Hz, 1H), 4.44 (q, 2H), 1.40 (t, 3H).

1. customThe ether was removed under vacuum and anhydrous toluene (80 mL)
2. additionwas added
3. stirringThe reaction mixture was stirred at rt for 15 h
4. stirringthe reaction mixture was stirred at rt for 1 h
5. customMost of the solvent was evaporated
6. additionEtOAc (60 mL) and water (40 mL) were added to the mixture
7. customThe layer was separated
8. washthe organic layer was washed with water (2×40 mL)
9. dry with materialdried over Na2SO4
10. filtrationfiltrated
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by column chromatography
13. washeluted with 20% EtOAc/hexane

ORD record

ord-f9b5ca20ea084fcb85dcaecd35367a30

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420066B2